Study on Tonghaosu and Its Analogs： Isolation, Structure Identification and Synthesis of Antifeedant B-ring-homo-tonghaosu

The methanolic extract from a Chinese endemic Chrysanthemum plant, Dendranthema indicum var. aromaticum, was found to show high antifeeding activity against Pieris brassicae L., and by bioassay-guided separation, the active component, B-ring-homo-tonghaosu, 2-(2‘,4‘-hexadiynylidene)-1,6-dioxaspiro-[4,5]-dec-3-ene (2) was isolated. Its structure was elucidated by comparing its spectroscopic data with those of 2 reported in the literatures. Furthermore new convenient total synthesis methods of B-ring-homo-tonghaosu were also developed to confirm its structure and make its further application in crop protection available. In addition, extensive comparison of spectroscopic data showed that the structure of compound 21 reported in literature should be revised to 2.     

Chemical Composition of Natural Hydrolates and Their Antimicrobial Activity on Arcobacter-Like Cells in Comparison with Other Microorganisms

Hydrolates obtained via the hydrodistillation and steam distillation of Lavandula angustifolia Mill., Syzygium aromaticum L., Foeniculum vulgare Mill., and Laurus nobilis L. were analyzed by gas chromatography with flame ionization detector (GC-FID) and gas chromatography coupled to mass spectrometry (GC-MS). Additionally, the hydrolates were evaluated for antimicrobial activity (disk-diffusion and microdilution method), influence on biofilm formation (Christensen method) and cytotoxicity of concentrated hydrolates against human cell lines (A549) by xCELLigence system. Using chemical analysis, 48, 9, 13 and 33 different components were detected in lavender, clove, fennel and laurel hydrolates, respectively. Lavender hydrolate contained the largest proportion of 1,8-cineol, linalool furanoxide, and linalool. The main components of laurel hydrolate were 1,8-cineol, 4-terpineol and α-terpineol. Fenchone and estragole were the most abundant in fennel hydrolate, and eugenol and eugenyl acetate in clove hydrolate. Concentrated hydrolates showed significant antimicrobial activity. Clove hydrolate was among the most antimicrobially active agents, most preferably against C. albicans, with an inhibition zone up to 23.5 mm. Moreover, concentrated hydrolates did not show any cytotoxic effect again8 st human A549 cells. In the presence of the non-concentrated hydrolates, significantly reduced biofilm formation was observed; however, with concentrated clove hydrolate, there was an increase in biofilm formation, e.g., of A. thereius, A. lanthieri, and A. butzleri. Research shows new findings about hydrolates that may be important in natural medicine or for preservation purposes.     

Headspace single drop microextraction coupled with microwave extraction of essential oil from plant materials

Headspace single drop microextraction (HS-SDME) coupled with microwave extraction (ME) was developed and applied to the extraction of the essential oil from dried Syzygium aromaticum (L.) Merr. et Perry and Cuminum cyminum L. The operational parameters, such as microdrop volume, microwave absorption medium (MAM), extraction time, and microwave power were optimized. Ten microliters of decane was used as the microextraction solvent. Ionic liquid and carbonyl iron powder were used as MAM. The extraction time was less than 7 min at the microwave power of 440 W. The proposed method was compared with hydrodistillation (HD). There were no obvious differences in the constituents of essential oils obtained by the two methods.     

Growth Restriction of Rhizoctonia solani via Breakage of Intracellular Organelles Using Crude Extracts of Gallnut and Clove

Plant diseases reduce crop yield and quality, hampering the development of agriculture. Fungicides, which restrict chemical synthesis in fungi, are the strongest controls for plant diseases. However, the harmful effects on the environment due to continued and uncontrolled utilization of fungicides have become a major challenge in recent years. Plant-sourced fungicides are a class of plant antibacterial substances or compounds that induce plant defenses. They can kill or inhibit the growth of target pathogens efficiently with no or low toxicity, they degrade readily, and do not prompt development of resistance, which has led to their widespread use. In this study, the growth inhibition effect of 24 plant-sourced ethanol extracts on rice sprigs was studied. Ethanol extract of gallnuts and cloves inhibited the growth of bacteria by up to 100%. Indoor toxicity measurement results showed that the gallnut and glove constituents inhibition reached 39.23 μg/mL and 18.82 μg/mL, respectively. Extract treated rice sprigs were dry and wrinkled. Gallnut caused intracellular swelling and breakage of mitochondria, disintegration of nuclei, aggregation of protoplasts, and complete degradation of organelles in hyphae and aggregation of cellular contents. Protection of Rhizoctonia solani viability reached 46.8% for gallnut and 37.88% for clove in water emulsions of 1000 μg/mL gallnut and clove in the presence of 0.1% Tween 80. The protection by gallnut was significantly stronger than that of clove. The data could inform the choice of plant-sourced fungicides for the comprehensive treatment of rice sprig disease. The studied extract effectively protected rice sprigs and could be a suitable alternative to commercially available chemical fungicides. Further optimized field trials are needed to effectively sterilize rice paddies.     

公丁香中多种金属元素的ICP-AES研究

探讨公丁香中多种金属元素的测定方法,采用湿法硝酸-双氧水进行消解,用电感耦合等离子体原子发射光谱法(ICP-AES)同时测定试样中钾、镁及多种微量元素铅、铜、铁、铬、锌、锰等的方法.其检出限为0.000 4～0.095 4μg·mL-1,变异系数为0.4%～4.9%,回收率在91.8%～112.2%,结果令人满意.发现中药公丁香中含有比较丰富的锰元素,微量元素在中药中可能起到一定的药理作用,用ICP-AES测定中药中微量元素以评价中药价值具有重要的意义.     

Analysis of Volatile Organic Compounds from Dendranthema indicum var. aromaticum by Headspace Gas Chromatography-Mass Spectrometry and Accurate Mass Measurement

The volatile organic compounds from flowers, leaves, and stems of Dendranthema indicum var. aromaticum, obtained through a static headspace technique, were analyzed by gas chromatography-mass spectrometry (GC-MS) and accurate mass measurement. The qualitative approach, comprising accurate mass measurement, retention index, and mass spectral search, was utilized to identify compounds. A total of 162 components were identified, representing 97.55–98.72% of the volatiles of individual samples. The principal chemical components in flowers were bornyl acetate (15.40%), α-phellandrene (14.18%), p-cymene (9.64%), camphor (9.54%), β-linalool (8.61%), and α-thujone (7.06%). In leaves, the main components were p-cymene (20.42%), bornyl acetate (20.41%), α-phellandrene (13.67%), and β-linalool (5.46%). As for stems, trans-β-farnesene (17.95%), germacrene D (12.89%), β-phellandrene (12.70%), β-caryophyllene (10.18%), and bicyclogermacrene (8.01%) were the dominant volatile compounds. Comparative studies on the volatiles from various species of genus Dendranthema indicated that Dendranthema indicum var. aromaticum contains significantly more aroma compounds than its morphologically similar species.     

Molecular Basis of the Therapeutical Potential of Clove (Syzygium aromaticum L.) and Clues to Its Anti-COVID-19 Utility

The current COronaVIrus Disease 19 (COVID-19) pandemic caused by SARS-CoV-2 infection is enormously affecting the worldwide health and economy. In the wait for an effective global immunization, the development of a specific therapeutic protocol to treat COVID-19 patients is clearly necessary as a short-term solution of the problem. Drug repurposing and herbal medicine represent two of the most explored strategies for an anti-COVID-19 drug discovery. Clove (Syzygium aromaticum L.) is a well-known culinary spice that has been used for centuries in folk medicine in many disorders. Interestingly, traditional medicines have used clove since ancient times to treat respiratory ailments, whilst clove ingredients show antiviral and anti-inflammatory properties. Other interesting features are the clove antithrombotic, immunostimulatory, and antibacterial effects. Thus, in this review, we discuss the potential role of clove in the frame of anti-COVID-19 therapy, focusing on the antiviral, anti-inflammatory, and antithrombotic effects of clove and its molecular constituents described in the scientific literature.     

Quantification through TLC‐densitometric analysis,repellency and anticholinesterase activity of the homemade extract of Indian cloves

The rise of the mosquitoes‐transmitted diseases, like dengue, zika and chikungunya in Brazil in the last years has increased concerns on protection against mosquitoes bites. However, the prohibitive prices of the commercially available repellents for the majority of the Brazilian population has provoked a search for cheaper solutions, like the use of the homemade ethanolic extract of Indian clove (Syzygium aromaticum L.) as repellent, which has been reported as quite efficient by the local press. In order to verify this, we performed here the quantification of the main components of this extract through high‐performance thin‐layer chromatography (HPTLC)–densitometry and evaluated its efficiency as a repellent and its acetylcholinesterase (AChE) inhibition capacity. Our results have proved HPTLC–densitometry as an efficient and appropriate method for this quantification and confirmed the repellency activity, as well as its capacity of AChE inhibition.     

In Vitro Assessment of the Cytotoxic and Antiproliferative Profile of Natural Preparations Containing Bergamot,Orange and Clove Essential Oils

Medicinal plants and essential oils (EOs), in particular, were intensively studied in recent years as viable alternatives for antiproliferative chemical synthetic agents. In the same lines, the present study focuses on investigating the effects of natural preparations (emulsions) based on EOs obtained from Citrus bergamia Risso (bergamot-BEO), Citrus sinensis Osbeck (orange-OEO), and Syzygium aromaticum Merill et L. M. Perry (clove-CEO) on different healthy (human immortalized keratinocytes—HaCaT and primary human gingival fibroblasts—HGF) and human tumor cell lines (human melanoma—A375 and oral squamous carcinoma—SCC-4) in terms of the cells’ viability and cellular morphology. The obtained results indicate that the CEO emulsion (ECEO) induced a dose-dependent cytotoxic in both healthy (HaCaT and HGF) and tumor (A375 and SCC-4) cells. OEO emulsion (EOEO) increased cell viability percentage both for HaCaT and A375 cells and had an antiproliferative effect at the highest concentration in HGF and SCC-4 cells. BEO emulsion (EBEO) decreased the viability percentage of SCC-4 tumor cells. By associating OEO with CEO as a binary mixture in an emulsified formulation, the inhibition of tumor cell viability increases. The E(BEO/OEO) binary emulsion induced an antiproliferative effect on oral health and tumor cells, with a minimal effect on skin cells. The non-invasive tests performed to verify the safety of the test compound’s emulsions at skin level indicated that these compounds do not significantly modify the physiological skin parameters and can be considered safe for human skin.